ETHYL 3-HYDROXYHEXANOATE Chemical Properties

Boiling point:

90-92 °C14 mm Hg(lit.)

Density 

0.974 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.428(lit.)

FEMA 

3545 | ETHYL 3-HYDROXYHEXANOATE

Flash point:

202 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

pka

14.45±0.20(Predicted)

color 

Colorless to Almost colorless

Odor

at 100.00 %. fruity grape burnt wood hay spicy pineapple cranberry dusty woody

Odor Type

fruity

biological source

synthetic

JECFA Number

601

LogP

1.04

CAS DataBase Reference

2305-25-1(CAS DataBase Reference)

NIST Chemistry Reference

Hexanoic acid, 3-hydroxy-, ethyl ester(2305-25-1)

EPA Substance Registry System

Ethyl 3-hydroxyhexanoate (2305-25-1)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29181990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

ETHYL 3-HYDROXYHEXANOATE Usage And Synthesis

Chemical Properties

Ethyl 3-hydroxyhexanoate has a fruity odor.

Chemical Properties

Colorless clear liquid. Very slight Iy soluble in water, soluble in alcohol and oils. Powerful, fresh-fruity-oily, siightly green odor. Fresh-fruity, light and powerfu), penetrating taste.

Occurrence

Reported found in citrus, grape, orange, grapefruit and tangerine juice, orange peel oil, pineapple, strawberry, cognac, Scotch whiskey, red and white wine, passion fruit, mango, quince, wood apple, mountain papaya, pawpaw and hog plum (Spondias mombins L.).

Uses

Ethyl 3-Hydroxyhexanoate is a general volatile organic compound which contributes to the scent and flavor profile of various fruits such as guava fruit and bananas.

Preparation

By esterification of bera-Hydroxy caproic acid, which is an isomer of Leucic acid. The acid can be obtained from Butyraldchyde by condensation with Bromo acetic ester in presence of Zinc catalyst.

Definition

ChEBI: A fatty acid ester that is the ethyl ester of 3-hydroxyhexanoic acid.

Taste threshold values

Taste characteristics at 80 ppm: sweet, fruity, grape with citrus notes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 269, 1974 DOI: 10.1021/jo00916a043

Synthesis

GENERAL STEPS: THF (200 mL) was added to a 500 mL round-bottomed flask pre-dried in an oven equipped with a 30 cm long condenser and kept open to the atmosphere.THF was used directly without further drying or purification. Subsequently, it was heated to reflux temperature (66°C) on a sand bath and the solvent was rapidly stirred using a magnetic stir bar. The condenser was temporarily raised and 6.5 g (0.1 mol, 2 eq.) of ZnO particles were added to the hot solvent. Next, n-butyraldehyde (0.1 mol) and ethyl bromoacetate (0.2 mol, 2 eq.) were added to the reaction mixture. The condenser was immediately reconnected to the round-bottom flask, at which point rapid boiling was observed. After allowing the reaction to reflux rapidly for 1 min, the reaction vessel was removed from the heat source and cooled to room temperature. For all substrates, the reaction was monitored by TLC (eluent: hexane-EtOAc, 80:20) within 20 minutes to confirm completion. Excess THF was removed under vacuum, and the brown oil obtained was dissolved in hexane and the reaction quenched with H2O to form a yellow precipitate. After filtering the mixture, the hexane layer was washed sequentially with H2O (100 mL), 1M HCl (2 × 50 mL), H2O (100 mL) and brine (50 mL), and then dried with Na2SO4. Finally, hexane was removed under vacuum to afford the target product ethyl 3-hydroxyhexanoate in 86% to 95% yield (see Table 1).

References

[1] Synthetic Communications, 2001, vol. 31, # 24, p. 3781 - 3789
[2] Journal of Organic Chemistry, 1982, vol. 47, # 25, p. 5030 - 5032
[3] Journal of Organic Chemistry, 1982, vol. 47, # 25, p. 5030 - 5032
[4] Synthesis (Germany), 2015, vol. 47, # 1, p. 79 - 82
[5] Organic Letters, 2003, vol. 5, # 20, p. 3615 - 3617

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